Crosslinkable coatings from phosphorylcholine-based polymers

Lewis, Andrew L.; Cumming, Zoie L; Goreish, Hind H.; Kirkwood, Laura C; Tolhurst, Lee A; Stratford, Peter W.

doi:10.1016/s0142-9612(00)00083-1

Cited by 181 publications

(124 citation statements)

References 20 publications

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“…16 Polycarboxybetaines and polysulfobetaines show good biocompatibility, [17][18][19][20] antibacterial properties and their utility for building bioinert coatings. [21][22][23][24] It is worth mentioning that the structure of sulfobetaine is similar to taurine, present in high concentration in animals and in trace concentration in plants. 25 Further glycine betaine, an analog of carboxybetaine is one of the solutes vital to the osmotic regulation of living organisms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of zwitterionic organogels based on Schiff base chemistry

Tarannum

Singh

2010

J of Applied Polymer Sci

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Poly(sulfobetaine)s and poly(carboxybetaine)s have been extensively studied for their zwitterionic and biocompatible nature. The specific features that make such zwitterionic structures technologically important are their chemical structure, a straight forward synthetic route, high ionic contents with interesting dilute solution, and solid state properties. The objective of this work is to synthesize novel zwitterionic polymers having gel characteristics. Here, p-phenylene diamine/melamine react as nucleophiles with glutaraldehyde to produce poly(schiff base)s. In the subsequent step, the poly(sulfobetaine)s and poly(carboxybetaine)s were produced on treatment with 1,3-propane sultone/c-butyrolactone. Hence, a catalyst free facile approach to novel zwitterionic polymers was obtained. The polymers were characterized by elemental analyses, FTIR, XRD analyses, SEM, pH metric titrations, conductometric titrations, and thermal analyses (TGA/ DTA). The polymeric samples carry the gel characteristics, showing lamellar structure with porous network. XRD pattern shows Bragg peaks indicative of superstructures. Thermal analysis indicates the Hoffman elimination of b hydrogen and subsequent release of sulfopropyl/carboxybutyl group. One of the gel polymers shows fluorescence also.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of zwitterionic organogels based on Schiff base chemistry

Tarannum

Singh

2010

J of Applied Polymer Sci

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“…21 As a typical hydrophilic monomer, 2-hydroxypropyl methacrylate (HPMA) has been used in various applications, including thermally crosslinkable paint formulations, surface modification of textile fibers, reactive adhesives and coatings, photo-resistants, and radiation curing. 22,23 In the viewpoint of steric hindrance, the HPMA oligomers or polymers should be bulky enough as end-capping groups of PRs.…”

Section: Introductionmentioning

confidence: 99%

Novel main‐chain polyrotaxanes synthesized via ATRP of HPMA in aqueous media

Zhang

Zhu

Tong

et al. 2008

J. Polym. Sci. A Polym. Chem.

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“…This discouraging finding can be explained at least in two ways: First the cells do not adhere on the phospholipid in general because the coating has a repulsive effect as it is known for PC-headgroup phospholipids used to produce blood compatible coatings (Ishihara et al, 1992;Iwasaki et al, 1999;Iwasaki et al, 2001;Korematsu et al, 2002;Lewis et al, 2001;Smeets et al, 1996;Zwaal et al, 1998). On the other hand it might be speculated that the cells can adhere to phospholipid coatings, but are then washed away with the underlying phospholipid layer which is only loosely bound to the metallic surface by hydrophobic and charge effects.…”

Section: Discussionmentioning

confidence: 99%

In-vitro interactions of human chondrocytes and mesenchymal stem cells, and of mouse macrophages with phospholipid-covered metallic implant materials

Willumeit¹,

Schossig²,

Clemens³

et al. 2007

eCM

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Phospholipid-coatings on metallic implant surfaces were evaluated in terms of adhesion, proliferation and matrix production of skeletal cells, and of macrophage stimulation. The working hypothesis is that mimicking a model biomembrane by phospholipids on surfaces to which cells adhere, the surface recognition by surrounding cells is altered. In this study, 1) mirror-like polished Ti-6Al-7Nb and 2) porous Ti-6Al-4V specimens were covered with the phospholipids POPE (palmitoyl-oleoyl phosphatidylethanolamine) and POPC (palmitoyl-oleoyl phosphatidylcholine), and the interactions of a) human articular chondrocytes (HAC), b) human mesenchymal stem cells (HMSC), and c) mouse macrophages (RAW 264.7) were tested in vitro.On POPE-covered polished surfaces adherence of HAC (42% of seeded cells after 2 hrs) and metabolic activity (MTT after 3 days) were reduced, while on porous surfaces 99% HAC adhered, and metabolic activity was significantly increased, compared to respective native surfaces. On both POPE-covered surfaces the chondrocyte phenotype was present. After 3 weeks of chondrogenic differentiation, cartilage matrix production (measuring chondroitin sulphate per HAC number) was significantly increased by about 30% on both POPE-covered metallic surfaces. On both POPCcovered surfaces nearly no adhering and surviving HAC were found.HMSC grown on POPE-covered porous substrates showed osteogenic differentiation by improved osteopontin and collagen I expression in RT-PCR, and osteocalcin fluorescence and bone nodule formation was only detectable on POPE-covered porous surfaces. In contrast to POPC and other phospholipids used as positive controls, POPE did not stimulate the NO production in mouse macrophage cultures. We therefore conclude that a phospholipid coating by POPE shows potential as surface modification for metallic implant materials.

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Crosslinkable coatings from phosphorylcholine-based polymers

Cited by 181 publications

References 20 publications

Synthesis and characterization of zwitterionic organogels based on Schiff base chemistry

Synthesis and characterization of zwitterionic organogels based on Schiff base chemistry

Novel main‐chain polyrotaxanes synthesized via ATRP of HPMA in aqueous media

In-vitro interactions of human chondrocytes and mesenchymal stem cells, and of mouse macrophages with phospholipid-covered metallic implant materials

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